Welcome to the forums.
Cubase offers what it calls “iterative” quantize. You may also record with Auto Quantize on or off.
Using Midi Modifiers as a MIDI Insert you may further “humanize” things with some randomness to pitch, velocity, position. If you like, you may assign a Key Command to Open/Close the Quantize Panel. I use Cltr-Shift-Q for it, but that’s up to your preference.
You can select notes within a track and apply different quantize values to selected notes. Selecting Notes can be done by hand in the Key Editor or with the Midi Logical Editor. You can also select measures on the Project Window and apply quantize to the measures selected.
I’ve seen some reports about issues with quantize, but, all in all, I’ve found the quantize functions in Cubase to be excellent and accurate.
Check these settings –
I don’t know Reaper so can’t speak to that. Good luck.